Acetic Acid → 8-(4-Chloro-benzenesulfonylamino)-4-[2-(pyridin-3-yloxy)-ethyl]-octanoic acid

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Reaction Steps

To a solution of 1.3 g (2.7 mmol) of ethyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoate in 8.1 ml acetonitrile is added 2.7 ml (5.4 mmol) 2M LiOH solution in water. After 18 h at room temperature, the reaction mixture is diluted with 9.5 ml water and filtered to remove a small amount of insoluble solid. The filtrate is acidified with 0.36 g (5.94 mmol) acetic acid and stirred in an ice bath. After 2 h the solid is filtered, washed with water and dried. Recrystallization from acetonitrile gives pure compound of example 31, namely 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl)-octanoic acid, m.p. 86°-88°; further recrystallization gives m.p. 89°-91°. Compound forms potassium salt as hydrate (containing 1.5 moles water).

Provenance & Evidence